Eastport Real Estate

Eastport Real Estate

Welcome to Eastport, a charming and vibrant subdivision nestled in the heart of Annapolis, Maryland. Known for its picturesque waterfront views and rich maritime history, Eastport offers a unique blend of coastal living and urban convenience, making it a coveted destination for homebuyers seeking both relaxation and community.

Eastport is characterized by its quaint streets lined with beautiful homes, many of which showcase classic architectural styles that reflect the area’s rich heritage. Residents enjoy a friendly, tight-knit atmosphere where neighbors know each other by name and community events foster a sense of belonging. With its close proximity to the Chesapeake Bay, Eastport is a paradise for boating enthusiasts, offering easy access to marinas and sailing opportunities.

The subdivision boasts an array of amenities, including local shops, delightful eateries, and vibrant art galleries, all within walking distance. Enjoy a leisurely stroll along the waterfront or partake in the lively atmosphere of the Eastport Yacht Club. For those who appreciate outdoor activities, nearby parks and walking trails provide ample opportunities for exploration and relaxation.

Eastport’s prime location means you’re just minutes away from Annapolis’ bustling downtown, where you can immerse yourself in history, culture, and entertainment. From the iconic Maryland State House to the lively farmers’ market, there’s always something to see and do.

With its stunning scenery, strong community spirit, and convenient access to urban amenities, Eastport is more than just a place to live; it’s a lifestyle waiting to be embraced. Come find your dream home in this enchanting Annapolis subdivision today!

Newest Listings in Eastport

$1,395,000
4 Beds ⋅ 5 Baths ⋅ MDAA2157002 MLS
Highly desirable Eastport location—just a short walk to Historic Annapolis, the U.S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multi‑generational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated three‑level Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main‑level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage—ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines here: a spacious deck and stone patio create inviting spaces for entertaining, grilling, or unwinding in a peaceful setting. With numerous exterior upgrades and a location that captures the best of Eastport living, this property is truly one of a kind.

1030 Boucher Ave, Annapolis
$1,050,000
2 Beds ⋅ 2 Baths ⋅ MDAA2155302 MLS
Highly Desirable Eastport Peninsula! Experience the best of the Eastport lifestyle in this charming home, ideally located in the heart of the peninsula. Relax on the inviting front porch and watch the world go by, or step out your door and walk to Eastport’s renowned restaurants, lively bars, boutique shopping, marinas, yacht clubs, and the water taxi to historic downtown Annapolis. Inside, beautiful heart pine floors add warmth and character. The spacious rear yard is a rare find in Eastport and offers plenty of room for entertaining, gardening, pets, or simply enjoying your own private outdoor retreat. The chef’s kitchen features Viking refrigerator and stainless steel appliances, creating a wonderful space for both everyday cooking and entertaining. Thoughtful improvements and major updates throughout the years make this home truly move-in ready while still offering the opportunity to add your own personal touches. Notable improvements include: * Pella rear sliding glass door — 2025 * Carrier first-floor HVAC — 2025 * Washer & dryer — 2024 * Viking refrigerator — 2024 * New roof — 2023 * First-floor bathroom remodeled — 2018 * Front porch replaced and metal roof added — 2018 * First-floor floors and stairs refinished by Beers — 2017 * Rinnai tankless water heater — 2016 * Upstairs bathroom and closet remodeled by Gate One Builders — 2011 * HardiePlank siding — 2009 * Fence — 2005 * Brick foundation repointed — 2004 * Shed — 2003 * Renovation and rear addition — 1998 A wonderful opportunity to own a piece of Eastport—move right in, enjoy the lifestyle, and make it your own.

412 Third St, Annapolis
$2,695,000
4 Beds ⋅ 4 Baths ⋅ MDAA2156250 MLS
Celebrate the Eastport lifestyle in this beautifully crafted home, where classic Craftsman character meets the comfort and ease of newer construction. Built in 2016 and lightly lived in, the home captures everything that makes Eastport so desirable, from its welcoming front porch, charming architectural details, and beautifully curated landscaping to a location just steps from marinas, restaurants, waterfront parks, and the vibrant streets of Downtown Eastport and Annapolis. Lush, thoughtfully designed landscaping brings the property to life, framing the home with color, texture, and greenery and creating an inviting sense of arrival. A gracious front porch sets the tone for the warm and welcoming interiors. Just inside, a dedicated office provides a quiet workspace, while hardwood floors, shiplap accents, custom millwork, and thoughtful details lend character throughout. The open floor plan unfolds into the heart of the home, where a spectacular kitchen features GE Monogram appliances, an expansive island, abundant cabinetry, and generous workspace. The adjoining dining area flows seamlessly into the living room, anchored by a fireplace framed with custom built-ins. Doors extend the living space to a large rear patio surrounded by beautiful landscaping, creating a private and inviting setting for outdoor dining, entertaining, and relaxed evenings at home. The main-level primary suite offers the convenience of one-level living with a beautifully appointed ensuite bath and conveniently located laundry room. A thoughtfully designed mudroom with built-in cubbies provides everyday functionality and an organized transition into the home. Additionally, the home features advanced technology throughout, including a Tesla Powerwall 3 for backup power, Tesla EV charger, and professionally installed Control4 home automation. The integrated system provides centralized control of lighting, climate, security, electronic locks, TVs, and built-in ceiling speakers throughout the home. Upstairs, two spacious bedrooms share a hall bath, while a large finished attic adds a wonderfully flexible dimension to the floor plan. Currently ideal as a bunk room, this charming bonus space can easily adapt as a playroom, additional sleeping quarters, creative studio, or whatever best suits your lifestyle. The finished lower level takes entertaining and recreation to another level with a spacious family room, game area, wet bar, full bath, and golf simulator. A separate bonus room currently serves as a home gym, while an expansive storage area provides the practical space that is often difficult to find in Eastport. Beyond the front door, the best of Annapolis is within easy reach. Launch a kayak from nearby Horn Point Park, stroll to Eastport's celebrated restaurants, pubs, marinas, and street-end parks, or cross the Spa Creek Bridge into Downtown Annapolis and the U.S. Naval Academy. Boaters will appreciate immediate proximity to the Chesapeake Bay and some of the region's most sought-after cruising destinations. Membership at the nearby Annapolis Capital Yacht Club marina also provides permission to enjoy the Chesapeake Landing community swimming pool, adding yet another way to embrace the waterfront lifestyle just steps from home. Offering the charm and personality of an Eastport Craftsman with the advantages of newer construction, beautiful landscaping, a main-level primary suite, exceptional entertaining spaces, and an enviable walkable location, this is a rare opportunity to experience one of Annapolis' most beloved neighborhoods with comfort, style, and ease. Welcome Home!

507 1st St, Annapolis
$1,925,000
4 Beds ⋅ 4 Baths ⋅ MDAA2156430 MLS
***Seller will consider owner financing*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

400 Jefferson St, Annapolis
$750,000
3 Beds ⋅ 3 Baths ⋅ MDAA2156278 MLS
Nestled in the charming Eastport neighborhood, this exceptional property blends warmth, character, and versatility. The main residence features 2 bedrooms and 1.5 bathrooms, with rich wood flooring, a cozy fireplace, and an inviting layout designed for comfortable living. A convenient basement laundry area and attached 1-car garage add everyday functionality. Step outside to discover even more possibilities, including a detached 1-bedroom, 1-bath guest house —perfect for guests, extended living, a home office, or additional storage. Set on a generous 0.17-acre lot, the property offers a wonderful balance of privacy, outdoor space, and neighborhood charm. With its desirable Eastport location, flexible living arrangements, and abundant character, this unique property offers an opportunity to enjoy both comfort and convenience in one of the area’s most appealing communities.

906 Jackson St, Annapolis
$1,875,000
4 Beds ⋅ 5 Baths ⋅ MDAA2156026 MLS ⋅ Sailor's Quay BLDG.
There is something unmistakably special about life in Eastport—and 820 Bay Ridge Ave captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence offers more than 4,000 square feet of sophisticated living across four beautifully finished levels, combining timeless architecture, thoughtful customization, and an effortless coastal sensibility just moments from the heart of Annapolis. Behind the white picket fence, manicured landscaping and gracious brick front porch create a picture-perfect welcome. Inside, rich hardwood floors, 9-foot ceilings, elegant millwork, tray ceilings, and plantation shutters establish a refined yet relaxed atmosphere. Unlike many homes in the community, this residence was thoughtfully customized during construction with numerous builder upgrades, enhanced electrical features, and details designed to improve both everyday living and long-term functionality. At the heart of the home, the beautifully appointed kitchen features honed granite countertops, premium appliances, abundant cabinetry, and a generous center island that opens seamlessly to the family room and its upgraded gas fireplace. The formal dining room, illuminated by a striking chandelier, is made for memorable dinners, while the adjoining sitting room or study is equally suited to a favorite book, working from home, or an evening bourbon. Outdoor living is woven beautifully into the home. Enjoy coffee on the charming front porch overlooking the flower garden, dinner in the private English courtyard, or cocktails on the second-floor terrace. Ceiling fans enhance both outdoor spaces, while a dedicated natural gas line makes grilling effortless and provides the opportunity for a future fire feature. Professionally enhanced landscaping and a thoughtfully improved yard complete this private outdoor retreat. The primary suite is serene and exceptionally spacious, with a custom walk-in closet, spa-inspired bath, and expansive private sitting room. A generous junior suite with its own bath offers wonderful privacy for family or guests, while two additional vaulted-ceiling bedrooms share a beautifully appointed full bath. The finished third-floor loft provides additional inviting spaces for a home office, fitness studio, media room, and guest retreat. The finished lower level adds a large family room and full bath, creating remarkable flexibility for entertaining, overnight guests, or multigenerational living. The home was also designed with the future in mind, with a framed elevator shaft allowing for the addition of an elevator without compromising its architecture or thoughtful floor plan. And then there is the location. This is the kind of Annapolis address where so much of daily life can happen on foot. St. Mary’s School, City Dock, neighborhood cafés, restaurants, boutiques and shopping are all within walking distance, as are the Annapolis Yacht Club and Eastport Yacht Club. Stroll to Eastport’s waterfront restaurants and marinas, cross the Spa Creek Drawbridge into Historic Downtown Annapolis, or take the water taxi home after an evening downtown. The United States Naval Academy, galleries, parks, sailing, and the unmistakable energy of the Chesapeake are all part of the lifestyle. Morning coffee at a neighborhood café. An afternoon on the water. Dinner in Eastport. A walk across the bridge for ice cream at City Dock. School, sailing, dining, shopping and downtown Annapolis—all without having to get in the car. This is polished Eastport living at its best: gracious but never fussy, luxurious yet wonderfully livable, and perfectly positioned to enjoy one of Annapolis’ most sought-after neighborhoods. With more than 4,000 square feet, four finished levels, exceptional outdoor spaces, extensive custom upgrades, future elevator capability, and an enviable Sailor’s Quay address, 820 Bay Ridge Ave offers a rare opportunity to enjoy Annapolis exactly as it was meant to be lived.

820 Bay Ridge Ave, Annapolis
$575,000
3 Beds ⋅ 2 Baths ⋅ MDAA2154778 MLS
There's history here. In the 1940s, the Meade family built a number of homes on President Street and in Hillsmere — Meade Street bears their name. For the first time, the family will be passing on this home, one of the last one still in family hands, to new owners. Original wood trim, high ceilings, and wood floors pair with a surprisingly open floor plan for its age. The third bedroom and kitchen were added in the 1960's. The daughters' bedroom was the upper level for many years. A detached garage with an attached screened porch is perfectly positioned for outdoor entertaining. The yard is large and fenced. This home only needs the new owner's personal touches to make it once again a forever home!

1309 President St, Annapolis
$599,900
3 Beds ⋅ 1 Baths ⋅ MDAA2155134 MLS
Eastport! Eastport! Eastport! Corner lot that consists of 9,240 square feet. Off street parking and street parking. Stainless steel refrigerator, stacked washer and dryer, storage in lower level off kitchen. New 10 foot by 15 foot shed. Separate dining room. Back porch is 21 feet by 7 feet. Partially fenced back yard. Upstairs bedroom has unique wood ceiling. Freshly painted living room, 2 bedrooms, and dining room. Lot has room for expansion. Close to downtown, Quiet Waters Park, and Eastport Shopping Center. Easy access to main streets.

1311 President St, Annapolis
$325,000
2 Beds ⋅ 2 Baths ⋅ MDAA2154860 MLS
Fee-simple living in the Eastport area, minutes from downtown Annapolis — for less than a citywide condo. This bright, easy-living two-bedroom, two-full-bath home sits on its own 0.08-acre lot — no condo fee, no HOA — and features a new roof. The primary suite opens through full-size sliding glass doors straight onto a private patio and backyard, while the kitchen draws light from two exposures plus a skylight, with a pass-through eat-in counter perfect for morning coffee. A dedicated laundry center and off-street parking pad add everyday ease. Out back, a shed provides real storage for bikes, tools, and seasonal gear. Convenient to downtown Annapolis and the Eastport area's restaurants. Vacant and easy to show. Photos have been virtually staged. Open house Saturday and Sunday, 2–4 PM.

1136 Tyler Ave, Annapolis
$725,000
6 Beds ⋅ 3 Baths ⋅ MDAA2154722 MLS
Welcome to 1025 Hanson Street, offering nearly 2,880 sq. ft. of exceptionally flexible living space across three finished levels in the heart of Annapolis! Perfect for a multi-generational family. Thoughtfully improved and meticulously maintained, this turn-key home provides a rare combination of space, versatility, parking and major system upgrades. The main and upper levels feature 4 bedrooms, a full bath, a bright and open living area, an updated kitchen with granite countertops and tile backsplash, and dedicated laundry with front-loading washer and dryer, utility sink and additional storage. The fully finished ground level creates an incredible second living space featuring 2 additional bedrooms, a den/office, full bath, kitchenette with granite countertops, stainless steel appliances and tile backsplash, a second laundry setup with utility sink, and new LVP flooring throughout. A private side entrance, new fencing, paver walkway and patio access provide tremendous flexibility for multi-generational living, extended guests, a home office setup or simply additional space to spread out. Outside, you'll find features that are especially hard to come by in Annapolis—including dual driveways with parking for 6+ vehicles and/or boats, along with a two-story detached shed offering excellent storage and convenient yard and street access. Extensive improvements provide peace of mind, including a NEW 2025 roof on both the home and shed with transferable warranty, updated HVAC including heat pump and indoor coil, 60-gallon hybrid high-efficiency water heater, 200-amp electrical service, Tesla EV charger, French drain and stormwater management system, sump pump, updated attic insulation with spray foam, Nest thermostats, updated siding, additional ground-level egress, ceiling fans, fresh paint and much more. With three finished levels, two distinct living areas, exceptional parking and storage, and numerous major capital improvements already completed, 1025 Hanson Street offers the kind of versatility that's difficult to find in Annapolis. Whether you're looking for room for a growing household, multi-generational living, extended guests, midshipman sponsor hosting, or simply a home that provides plenty of space to live, work and entertain—this one is a 10/10!

1025 Hanson St, Annapolis
$1,875,000
6 Beds ⋅ 5 Baths ⋅ MDAA2149696 MLS
** Private first-look appointments are available. Contact the listing agent to schedule for a first-look. ** A rare find in Eastport: an oversized attached two-car garage, plus a driveway and additional off-street parking, in a walkable waterfront neighborhood where garages are hard to come by. Beyond the striking exterior is a brand-new, ground-up home spanning three expansive levels, featuring 6 bedrooms, 4.5 baths, a chef-inspired kitchen with an oversized island and walk-in pantry, a main-level bedroom, an impressive primary suite, upper-level laundry, and a third-floor loft ideal for an office, guest space, or studio. Outside, enjoy a fully fenced yard, patio, and covered front porch — all just a short walk from Eastport’s marinas, restaurants, waterfront lifestyle, and downtown Annapolis.

914 Van Buren St, Annapolis
$750,000
3 Beds ⋅ 3 Baths ⋅ MDAA2151298 MLS
Welcome to Eastport. This three-bedroom and three-full-bath home, plus a lower-level den that easily serves as an on-suite; is a beautifully maintained, turn-key home offering over 2,000 square feet of fully finished living space. Originally transformed during a massive, studs-out 2017 remodel, this home offers ultimate peace of mind with entirely replaced core systems and premium finishes throughout. The chef’s kitchen is fully equipped with Saint Cecilia granite counter tops, an expansive island breakfast bar, premium stainless steel appliances, a mosaic tile back splash, and soft-close cabinetry. The open floor plan main level also includes 2 bedrooms and a full bathroom. Upstairs, a massive second-story addition houses a luxurious primary suite with a custom glass shower, a walk-in closet, and a sitting area. The lower level offers a family room with a storage area and a "DEN" with a full bath. No detail was spared in the renovation, which features gleaming new hardwood floors, energy-efficient double-pane tilt-in windows, and updated insulation. Enjoy worry-free living with a comprehensive HVAC setup including a gas furnace and central A/C, updated plumbing, new electrical panels, a new water heater, and a fully integrated, code-compliant interior fire sprinkler system. The exterior shines with architectural roof shingles, low-maintenance vinyl siding, new gutters, and a spacious gravel driveway. Outside, enjoy outdoor entertaining in the fully fenced, private backyard. Perfectly situated moments from historic downtown Annapolis, Eastport restaurants, and local waterways. Move right in and enjoy seamless coastal living!

907 Monroe St, Annapolis
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